Ethyl levulinate → 1H-Pyrrolo(1,2-a)imidazole-2,5(3H,6H)-dione, dihydro-7a-methyl-

HRID 344741

反応式

HRID 344741 の反応式
Cl.[NH2:2][CH2:3][C:4]([NH2:6])=[O:5].[OH-].[Na+].O=[C:10]([CH3:18])[CH2:11][CH2:12][C:13](OCC)=[O:14]>O>[O:5]=[C:4]1[CH2:3][N:2]2[C:13](=[O:14])[CH2:12][CH2:11][C:10]2([CH3:18])[NH:6]1

参加物

5

反応物 3

HCID 10883Ethyl levulinateHCID 14798Sodium HydroxideHCID 2723639Glycinamide hydrochloride

生成物 1

HCID 30795901H-Pyrrolo(1,2-a)imidazole-2,5(3H,6H)-dione, dihydro-7a-methyl-収率 21%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a solution of glycinamide hydrochloride (18.4 g, 0.166 mol) in water (200 ml), adjusted to pH 9.5 with 10% sodium hydroxide (about 60 ml), ethyl 4-oxopentanoate (20 g, 0.139 mol) was added. The solution was refluxed for 24 hours. After cooling the solvent was evaporated under vacuum and the residue was chromatographed over silica gel (dichloromethane-methanol 9:1) to afford 4.5 g (21%) of the title compound, m.p. 187°-189° C. NMR (CDCl3): deltaH =4.17 and 3.53 (ABq, J=16 Hz, 2H, NCH2CO), 1.5 (s, 3H, CH3). MS (E.I., 70 eV, 1.5 mA) m/z=154 (M+), 139 (M--CH3)+, 111 (M--CONH)+.

後処理

  1. additionwas added
  2. temperatureThe solution was refluxed for 24 hours
  3. temperatureAfter cooling the solvent
  4. customwas evaporated under vacuum
  5. customthe residue was chromatographed over silica gel (dichloromethane-methanol 9:1)

出典と根拠

ORDレコード
ord-6ad2ce07f5384ac7a74581258ecdfb37
出典データセット
uspto-grants-1991_10
特許番号
US05053422

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